Synthesis of colorants in mixing apparatus
A process for preparing colorants of the general formula (Ia), (Ib) or (Ic) or mixtures thereof, comprises reacting (a) tetracarboxylic acids or their functional derivatives with (b) at least one compound selected from i. aliphatic amines, ii. aromatic amines, iii. aliphatic diamines, iv. aromatic diamines, (c) optionally in the presence of further additives, (d) optionally in the presence of wetting agents in a mixing apparatus. These colorants are useful for coloration of macromolecular organic and inorganic materials of natural and synthetic origin.
1. A process for preparing a colorant of formula (Ia), (Ib) or (Ic), the process comprising:
reacting, in a mixing apparatus, a reaction mixture comprising
(a) a tetracarboxylic acid or an anhydride, bisanhydride, an acid chloride, or a salt of the tetracarboxylic acid, with a base comprising
(b) at least one selected from the group consisting of
(b1) an aliphatic amine,
(b2) an aromatic amine,
(b3) an aliphatic diamine, and
(b4) an aromatic diamine,
to obtain a product compound of formula (Ia), (Ib), or (Ic), or a mixture thereof
wherein
R 1 and R 2 are the same or different and independently represent phenylene, naphthylene, pyridylene,
and R 1 and R 2 each are optionally substituted one or more times by at least one substituent selected from the group consisting of C 1 -C 22 -alkyl, C 3 -C 22 -alkenyl, C 1 -C 22 -alkoxy, hydroxyl, nitro, and halogen,
R 3 and R 4 are the same or different and independently represent hydrogen, C 1 -C 22 -alkyl, aryl, C 1 -C 22 -aralkyl,
Q: C 1 -C 20 -alkyl, aryl
and R 3 and R 4 each are optionally substituted one or more times by at least one substituent selected from the group consisting of C 1 -C 22 -alkyl, C 1 -C 22 -alkoxy, hydroxyl, nitro, and halogen,
X in each occurrence is the same or different and independently represents halogen,
n and p are independently 0, 1, 2, 3, or 4, and
m is 0, 1, 2, 3, or 4
wherein the mixing apparatus is a kneader-like reactor, a single-shaft kneader, or a multi-part/shaft kneader,
wherein the reacting is carried out in the presence of at most 100 wt. % of (d) a wetting agent, based on a total weight of all other components in the reaction mixture, and
wherein the reacting is carried out in no solvent other than said wetting agent.
2. The process of claim 1 , further comprising:
further processing the product compound in the form of a resulting crude pigment in the mixing apparatus.
3. The process of claim 2 , wherein the further processing is effected by salt kneading.
4. The process of claim 2 , wherein the further processing is effected in the presence of (c) an additive, in an amount from 1% to less than 50% by weight, based on a weight of components (a) and (b) in the reaction mixture.
5. The process of claim 4 , wherein the wetting agent (d) is present in an amount of up to 90% by weight, based on a weight of components (a), (b), and (c) in the reaction mixture.
6. The process of claim 1 , wherein R 1 and R 2 are the same and each represent unsubstituted phenylene or naphthylene.
7. The process of claim 1 , wherein R 3 and R 4 are the same and each represent alkoxyphenyl, methyl, propyl, 2,4-dimethylphenyl, hydrogen or
8. A method for coloring a macromolecular organic or inorganic material of natural and synthetic origin, comprising:
combining with the material, the product made by the process of claim 1 .
9. The process of claim 1 , further comprising:
coloring a plastic, a paint, or a printing ink with the colorant.
10. The process of claim 1 , wherein the base comprises (b1) the aliphatic amine.
11. The process of claim 1 , wherein the base comprises (b2) the aromatic amine.
12. The process of claim 1 , wherein the base comprises (b3) the aliphatic diamine.
13. The process of claim 1 , wherein the base comprises (b4) the aromatic diamine.
14. The process of claim 1 , wherein R 1 is phenylene.
15. The process of claim 1 , wherein R 1 is naphthylene.
16. The process of claim 1 , wherein the wetting agent (d) is at least one selected from the group consisting of a glycol, a fatty alcohol, a sulfone, a sulfoxide, diacetone alcohol, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, butyl acetate, and glycerol triacetate.
17. The process of claim 1 , wherein the wetting agent (d) comprises a glycol.
18. The process of claim 1 , wherein the wetting agent (d) comprises at least one selected from the group consisting of triglycol and tetraglycol.
19. The process of claim 1 , wherein the wetting agent (d) is present in an amount of up to 57.3% by weight, based on a weight of components (a) and (b) in the reaction mixture.
20. The process of claim 4 , wherein the additive (c) comprises at least one selected from the group consisting of a secondary amine and a tertiary amine.